US4447244A - Process for mass-dyeing of thermoplastics: polystyrene and styrene copolymers with indoline methine dyes - Google Patents
Process for mass-dyeing of thermoplastics: polystyrene and styrene copolymers with indoline methine dyes Download PDFInfo
- Publication number
- US4447244A US4447244A US06/464,073 US46407383A US4447244A US 4447244 A US4447244 A US 4447244A US 46407383 A US46407383 A US 46407383A US 4447244 A US4447244 A US 4447244A
- Authority
- US
- United States
- Prior art keywords
- sub
- designates
- alkyl
- methyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000004043 dyeing Methods 0.000 title claims abstract description 12
- 239000000975 dye Substances 0.000 title claims description 15
- 239000004793 Polystyrene Substances 0.000 title claims description 12
- 229920002223 polystyrene Polymers 0.000 title claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 9
- 229920001577 copolymer Polymers 0.000 title claims description 9
- 229920001169 thermoplastic Polymers 0.000 title abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 title abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- -1 sulphamoyl Chemical group 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000000460 chlorine Chemical group 0.000 claims description 12
- 229910052801 chlorine Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 101100177155 Arabidopsis thaliana HAC1 gene Proteins 0.000 claims 1
- 101100434170 Oryza sativa subsp. japonica ACR2.1 gene Proteins 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 238000000465 moulding Methods 0.000 description 10
- 239000008187 granular material Substances 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FDVITFMRUUGIBF-UHFFFAOYSA-N 2-methylidene-1,3-dihydroindole Chemical class C1=CC=C2NC(=C)CC2=C1 FDVITFMRUUGIBF-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
Definitions
- the invention relates to a process for mass-dyeing of thermoplastics, which is characterised in that the dyestuffs used are of the formula ##STR3## in which
- R designates hydrogen or alkyl
- R 1 and R 2 designate alkyl
- R 3 designates hydrogen, cyano, aroyl, alkoxycarbonyl, alkylcarbonyl or carbamoyl,
- R 4 designates aryl
- R 5 designates alkyl, alkylcarbonyl, alkoxycarbonyl or aryl
- R 6 designates alkyl, aryl, aralkyl or aralkenyl
- Y designates O or NR 7 , with R 7 having the meaning hydrogen, alkyl, aralkyl or aryl, it being possible for the radicals which have been mentioned for R 7 and R 1 -R 7 and which contain C--H or N--H bonds to be substituted, and wherein the ring A can carry 1, 2 or 3 substituents from the series comprising halogen, cyano, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, carbamoyl, sulphamoyl, alkylsulphonyl and arylsulphonyl, or can have a benzene ring fused to it, it being possible for the radicals which have been mentioned as substituents of the ring A and which contain C--H or N--H bonds to be substituted.
- R' designates hydrogen, methyl or ethyl
- R 1 ' and R 2 ' designate methyl or ethyl
- R 3 ' designates hydrogen, cyano, aroyl, in particular benzoyl and naphthoyl, alkoxycarbonyl, in particular (C 1 -C 4 -alkoxy)-carbonyl or carbamoyl,
- R 4 ' designates phenyl which can be substituted by methyl, ethyl, methoxy, ethoxy or chlorine,
- R 5 ' designates methyl, methoxycarbonyl or ethoxycarbonyl, or phenyl wich can be substituted by methyl and/or ethyl,
- R 6 ' designates C 1 -C 4 -alkyl, phenyl, chlorophenyl or methylphenyl, or phenyl-C 1 -C 3 -alkyl which can be substituted in the phenyl nucleus by chlorine and/or methyl, or designates phenylallyl or phenoxyethyl,
- Y' designates O or NR 7 , wherein
- R 7 ' represents alkyl, in particular C 1 -C 4 -alkyl, or aralkyl, in particular phenyl-C 1 -C 3 -alkyl
- L designates hydrogen, chlorine, cyano, methyl, ethyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl or benzyloxycarbonyl, or sulphamoyl or carbamoyl which is optionally substituted by methyl, ethyl or phenyl, or designates methylsulphonyl or phenylsulphonyl
- M and Q designate hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or methoxycarbonyl, and two of the substituents L, M and Q together can form a fused benzene ring.
- R' designates hydrogen or methyl
- R 1 ' and R 2 ' designate methyl
- R 3 ' designates hydrogen, cyano or benzoyl
- R 4 ' designates phenyl which can be substituted by methyl, methoxy and/or chlorine
- R 5 ' designates methyl or methoxycarbonyl
- L designates hydrogen, methoxycarbonyl, cyano, methoxy or chlorine
- R 6 ' designates C 1 -C 4 -alkyl, phenyl, chlorophenyl or methylphenyl, or phenyl-C 1 -C 3 -alkyl, the phenyl radical of which can be substituted by chlorine or methyl, or designates phenoxyethyl.
- the compounds ##STR7## are very particularly preferably employed in the process according to the invention.
- the methine dyestuffs to be used according to the invention represent known compounds.
- the dyestuffs of the general formula Ia are advantageously prepared by condensation of pyrazolone-4-aldehydes of their N,N-dialkylsubstituted enamines with the appropriate 2-methyleneindolines (see German Auslegeschrift No. 1,154,894), or by reaction of 2-methyleneindoline- ⁇ -aldehydes with the appropriate pyrazolone (see German Auslegeschrift No. 1,172,487).
- the compounds of the formula Ib are obtained by condensation of the 2-methyleneindoline- ⁇ -aldehydes with the appropriate cyanoacetates (see German Auslegeschrift No. 1,172,387 or 1,569,728).
- the dyestuffs listed in Table 2 below dye polystyrene yellow when used in customary mass-dyeing processes.
- thermoplastics such as cellulose esters, such as cellulose nitrate, cellulose acetate, cellulose triacetate, cellulose acetobutyrate and cellulose propionate, cellulose ethers, such as methylcellulose, ethylcellulose, and benzylcellulose, polyethylene terephthalate, linear saturated polyester resin plastics, polyamides, aniline resin plastics, polycarbonates, polyethylene, polypropylene, polystyrene, polyvinylcarbazole, polyvinylchloride, in particular rigid PVC, polyisobutylene, polymethacrylates, polyvinylidenechloride, polytetrafluoroethylene, polytrifluoroethylene, polyacrylonitrile, polyoxomethylenes, linear polyurethanes, polyphenylene oxide, polysulphones and copolymers, such as vinyl chloride/vinyl acetate copolymers and in particular styrene copolymers, such as
- the new process is particularly suitable for mass-dyeing polystyrene and styrene copolymers, in particular ABS.
- the dyeings obtained are distinguished by good light fastnesses and weathering fastnesses.
- the dyestuffs according to the invention possess, in the thermoplastics, extremely high thermal stabilities and stabilities to sublimation.
- the dyestuff of the formula (IV) can be employed in ABS even at temperatures above 280° C. without noticeable changes in shade occurring or it being possible to detect sublimation.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823206091 DE3206091A1 (de) | 1982-02-19 | 1982-02-19 | Verfahren zum faerben thermoplastischer kunststoffe in der masse |
| DE3206091 | 1982-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4447244A true US4447244A (en) | 1984-05-08 |
Family
ID=6156230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/464,073 Expired - Lifetime US4447244A (en) | 1982-02-19 | 1983-02-04 | Process for mass-dyeing of thermoplastics: polystyrene and styrene copolymers with indoline methine dyes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4447244A (enrdf_load_html_response) |
| EP (1) | EP0087044A1 (enrdf_load_html_response) |
| JP (1) | JPS58152054A (enrdf_load_html_response) |
| DE (1) | DE3206091A1 (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5507737A (en) * | 1993-04-22 | 1996-04-16 | Siemens Elema Ab | Apparatus for determining the volume of a bellows reservoir for medication in an implantable infusion system |
| US11193023B2 (en) * | 2018-10-09 | 2021-12-07 | Lanxess Deutschland Gmbh | Methine dyes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2739352B2 (ja) * | 1989-09-22 | 1998-04-15 | 住化ファインケム株式会社 | メチン系化合物及びその用途 |
| DE10111731A1 (de) * | 2001-03-09 | 2002-09-12 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen Methinfarbstoffen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2840443A (en) * | 1954-08-05 | 1958-06-24 | Gen Aniline & Film Corp | Use of methylidyne bis pyrazolones for dyeing |
| DE1569728A1 (de) * | 1964-05-12 | 1970-05-14 | Bayer Ag | Methinfarbstoffe und Verfahren zu deren Herstellung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL135944C (enrdf_load_html_response) * | 1958-08-22 | |||
| DE1172387B (de) * | 1958-08-22 | 1964-06-18 | Bayer Ag | Verfahren zur Herstellung von Methinfarbstoffen |
| DE1567728B2 (de) * | 1965-06-22 | 1973-04-12 | Dr. C. Otto & Co Gmbh, 4630 Bochum | Verfahren zur erzeugung eines an wasserstoff und kohlenstoff reichen gases aus kohlendestillationsgasen |
-
1982
- 1982-02-19 DE DE19823206091 patent/DE3206091A1/de active Granted
-
1983
- 1983-02-04 US US06/464,073 patent/US4447244A/en not_active Expired - Lifetime
- 1983-02-07 EP EP83101117A patent/EP0087044A1/de not_active Withdrawn
- 1983-02-15 JP JP58022257A patent/JPS58152054A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2840443A (en) * | 1954-08-05 | 1958-06-24 | Gen Aniline & Film Corp | Use of methylidyne bis pyrazolones for dyeing |
| DE1569728A1 (de) * | 1964-05-12 | 1970-05-14 | Bayer Ag | Methinfarbstoffe und Verfahren zu deren Herstellung |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5507737A (en) * | 1993-04-22 | 1996-04-16 | Siemens Elema Ab | Apparatus for determining the volume of a bellows reservoir for medication in an implantable infusion system |
| US11193023B2 (en) * | 2018-10-09 | 2021-12-07 | Lanxess Deutschland Gmbh | Methine dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3206091A1 (de) | 1983-09-01 |
| JPS58152054A (ja) | 1983-09-09 |
| DE3206091C2 (enrdf_load_html_response) | 1991-10-31 |
| EP0087044A1 (de) | 1983-08-31 |
| JPH0449574B2 (enrdf_load_html_response) | 1992-08-11 |
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